


Boat Trip

by mnwood



Series: When Harry Met Sally 'Verse [4]
Category: Supernatural RPF
Genre: Family Dynamics, Foursome - F/F/M/M, Multi, POV Jensen, Pegging, Recreational Drug Use, Threesome - F/M/M, Vacation, Voyeurism
Language: English
Status: Completed
Published: 2017-08-23
Updated: 2017-08-23
Packaged: 2018-12-16 23:54:09
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,887
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11839656
Author URL: https://archiveofourown.org/users/mnwood/pseuds/mnwood
Summary: The Ackles and Collins families go on a boat trip together.





	Boat Trip

“Can I try the double chocolate and the, uh, dark chocolate brownie?”

Misha laughs and then quickly stops himself when Jensen glares at him.

“What?” Misha asks as the girl across the counter hands Jensen his samples. “You always get chocolate.”

“Well, I love chocolate, so get off my back.”

The girl hides a smile before turning to Misha and asking what samples he’d like to try.

“See, now she’s laughing at us,” Jensen says before licking his double chocolate ice cream off his tiny spoon. “Because you’re a jerk.”

“I’d like to try the pistachio, please,” Misha says, ignoring Jensen.

As the girl scoops out the pistachio ice cream, she responds, “Would you guys mind, um, taking a—taking a picture with me? After you get your ice cream.”

“Of course, sweetheart,” Jensen replies with a wink. “And I’ll have a large waffle cone with the dark chocolate brownie and chocolate sprinkles.”

“You know what, give him a chocolate waffle cone, too,” Misha says derisively. “I don’t think he has enough chocolate.”

“Oh yeah, if you’ve got a chocolate waffle cone I’ll take it,” Jensen says.

Jensen doesn’t really care about getting a chocolate waffle cone, but he won’t let Misha win this stupid game they’re playing. When Misha frowns at him and doesn’t say anything else, Jensen can’t help but smile at his victory.

After they get their ice cream, they each take a picture with the employee and then head outside to rejoin their wives and kids.

“She’s gonna put those pictures online,” Misha says in a low tone as they walk outside.

“So?”

“So, people are gonna know that we hung out.”

Jensen snorts back a laugh. “Who cares, Mish?”

“Who cares about what?” Vicki asks, looking between the two of them as she licks her ice cream cone.

“The girl in the store asked for our picture, and Misha here thinks it’s bad if people find out we’re hanging out together.”

Danneel and Vicki both laugh. Danneel says, “God forbid you hang out with your friends outside of work.”

Misha ignores them in favor of scooping Maison up onto his hip and letting her try his ice cream even though she already has her own.

When West sees Maison eating Misha’s ice cream, he runs up to Jensen and lifts his arms to be picked up.

“What’s up, Westy?” Jensen asks as he puts him on his hip.

“I wanna try the chocolate,” West replies.

Jensen offers his cone, and West grabs onto it eagerly. When he’s done, he says, “Thanks, Uncle Jensen!” before squirming out of his hold and running off to play some more.

“Y’all are both huge pushovers,” Danneel says.

Jensen and Misha both nod in response.

“Alright, well, we need to head out to the boat soon. We’re losing daylight,” Vicki says without making any moves to leave.

 _“Some_ body just _had_ to have ice cream,” Jensen teases.

Danneel flips him off as she licks her ice cream.

It’s a short trip out to the marina to get Misha’s boat, but four adults and three children crammed into a minivan doesn’t really make for an easy ride, no matter how short it is. Misha is short-tempered by the time they pile out, so Jensen and Danneel hang back and hold J.J.’s hands between them so the Collins family can sort their shit out ahead of them.

Everyone is relatively calm by the time they get to the boat, so the kids hang out around the dock pointing at different fish they can see in the shallow water while the adults unbutton the boat cover.

“I set out some crab traps earlier,” Misha says as he stuffs the boat cover under some seat cushions. “We should probably go check them, see if we have anything we can take home for dinner.”

As Misha is talking, Maison falls to her hands and knees on the dock and vomits her ice cream directly into the lake.

“Uh-oh,” Jensen says, jogging over to her and putting a hand on her back. “You OK, sweetheart?”

Maison shakes her head and begins to cry.

Vicki runs over and scoops Maison up into her arms. “It’s OK, Mais, we can go up to the marina and go potty.”

“I’ll go with you,” Danneel says, putting her unopened beer back in the cooler and climbing easily out of the boat.

“Well, should we all go?” Jensen asks.

“No, no,” Vicki responds. “You guys go ahead and check the crab traps. There’s a playground up there, so we’ll just hang out until you get back.”

Misha looks like he wants to argue, but Vicki gives him a look that makes him untie the boat from the dock and hop back on. Jensen picks up J.J. and quietly asks her if she’d rather go on the boat with him or up to the playground with Mom, and she points at the boat. He says, “Good girl,” as he puts her on the boat.

“I guess it’s just us then,” Jensen says as he puts life jackets on J.J. and West.

“Yeah. Uh,” Misha responds awkwardly. “I’m not sure we’re going anywhere.”

“What’s wrong?” Jensen looks up to see Misha in the driver’s seat fiddling with the controls.

“It’s OK, I think I have the number for, like, boat Triple A.”

Jensen climbs the ladder up to the top deck and takes a seat next to Misha. “What, it’s not starting?”

“No. Something must be wrong.” He hits a button a little too hard in frustration.

Jensen instinctively reaches a hand out and rubs between Misha’s shoulder blades. Misha twitches his shoulder in annoyance, a sign for Jensen to get off of him.

"I'm gonna go check the engine," Misha says as he heads for the ladder. 

Jensen watches him go, then he turns to the controls wondering if Misha put it in neutral. He huffs a laugh as he realizes Misha's mistake, then he puts it in neutral and turns the key. The boat roars to life.

Misha looks up from down below, his arms raised in the air and a frustrated look on his face.

"You forgot to put it in neutral," Jensen calls down.

Misha rolls his eyes and heads back toward the ladder. As he comes up, he says, "I  _swear_ I put it in neutral."

“You sure you know how to drive this thing?” Jensen teases.

 _“Yes,_ I know how to drive it.”

As they cruise out of the dock area, Misha accidentally bumps into a parked boat. He curses and refuses to let Jensen take over driving.

So instead, Jensen goes down on the main deck to play with the kids. They’re in a much better mood than Misha.

When they get to the crab traps, they pull up three decently-sized crabs and put two of them in a bucket. Misha gives West the third because he begged for it. Because they’re out of the main channel, they decide to park the boat for a minute and drink some beer up on the top deck while their kids play on the lower deck.

“You think Maison’s OK?” Jensen asks after a solid two minutes of silence.

Misha digs his phone out of his back pocket and looks at it for a second. He then says, “Yeah, she’s good. They’re wondering when we’re coming back.”

“I was hoping we could, you know, chill out here for a few minutes.”

“Yeah, I guess we can,” Misha says around a sigh.

“Hey.” Jensen leans over and smacks Misha in the arm. “Cheer up. We’re on a boat.”

Misha glares at him, but it only lasts a second before a smile pulls at his lips. He looks away and drinks his beer.

“Hey. Come here,” Jensen tries again.

But instead of Misha coming over to him, Jensen ends up going over to Misha and draping himself over the back of his chair. He wraps his arms around his chest and kisses his cheek, holding him tight.

Misha hums and reaches his hand up to latch onto Jensen’s forearm. He rubs his thumb against his skin and rests his head against Jensen’s cheek for a minute.

And then J.J. shrieks and the moment is gone.

As Jensen takes care of the restless kids, Misha starts the boat back up and tries to get going. About three minutes pass before Jensen realizes they haven’t moved at all.

“What is it now, Mish?” Jensen calls up to the top deck.

Misha looks down at him and throws his arms up in the air, annoyed. “Who knows.”

Jensen puts J.J. up on his hip and then follows Misha to the back of the boat to check out the propellers.

“I bet we’re stuck in the ropes from the crab traps,” Jensen says. “We pulled them up from here.”

“Yeah, that’s probably what it is.” Misha puts his knee up on the seat and his hands on the back of the boat and leans over as far as he can.

Jensen stares at his ass and licks his lips. He hikes J.J. up a little higher on his hip.

“I can’t see anything,” Misha says as he straightens back up and catches Jensen staring. He rolls his eyes. “Now’s not the time, babe.”

“You’re the one who put your butt in my face,” Jensen mumbles as he sets J.J. back down.

Misha pulls out his phone and fiddles with the case. “This is a waterproof case, so I’ll just put this under and see if I can video what’s going on.”

It’s the first time in the past couple of hours that Misha’s sounded optimistic. Jensen fights a smile, knowing that if he shows Misha any affection right now that he will probably punch him in the face.

After a minute of holding his phone underwater, Misha takes a look at it and immediately declares, “Alright, can’t see shit.”

He then takes his shirt off.

“What are you doing?” Jensen asks.

“I’m just gonna swim under and see if I can unhook the ropes.” He pulls one of the seats up and digs out a pair of goggles. “We can’t stay out here all day.”

As a way of distracting himself from Misha’s tanned and naked torso, Jensen leans over the back of the boat and fiddles with the ropes. It takes him two seconds to untangle them from the propellers.

“Alright, I got it,” he says casually.

Misha glares at him, giant goggles stuck to his face.

“What?” Jensen asks.

“Nothing.” He tears the goggles off and reaches for his shirt. “Let’s get going.”

On the trip back to the dock, Jensen stays with the kids and shoots a text to Danneel.

**_Mish is in a bad mood. We’re on our way back now._ **

She replies, _Why’s he in a bad mood?_

**_Don’t know. We’ll need to cheer him up when we get back to the house :)_ **

_Oh yeah? WE?_

**_;)_ **

“Jensen, need you on ropes,” Misha calls from up top.

Jensen quickly puts his phone away and says, “Yes, sir,” as he reaches for a buoy to throw over the side before they pull into the dock.

For the first time all day, nothing goes wrong. They get the boat tied up with no problems, and they elect not to cover it yet because they’ll probably go back out with Vicki and Danneel and Maison.

As they’re walking up to the playground, Misha smacks Jensen’s ass hard and growls in his ear, “You can’t just call me ‘sir’ when I can’t do anything about it.”

“Well, you can’t take your clothes off when _I_ can’t do anything about it,” Jensen fires back despite the racing of his heart.

“Hmm. Alright.” 

“We’ll do something about it later, Mish.”

“Yeah, we better.”

When they meet back up with their wives, Misha relays the story about getting stuck in the traps and Jensen “saving the day” _after_ Misha had stripped down in order to jump in.

“Oh, of course he did,” Danneel says, laughing hard.

“Hey, I was just trying to help! I didn’t know he was gonna...take his clothes off,” Jensen replies as Danneel and Vicki both laugh at him.

Misha is squatting in front of Maison scrutinizing her and asking her a million questions that sum up with, “Are you _sure_ you’re OK to go on the boat?”

Only a few minutes later they find themselves back on the boat, Misha already in much better spirits with his wife and Maison around. He insists that they take some pictures for Twitter, which Jensen obliges because that’s the kind of stupid shit people do when they’re in love. He doesn’t even argue when Misha calls him “cabin boy” to his two million followers.

It gets colder as the sun goes down, so Jensen puts on a jacket and hat and curls up with Danneel at the back of the boat while Misha drives them all around the lake.

Just before sunset, Misha parks the boat and pulls blankets out from under the seats. They all sit on the lower deck together and drink beer while the kids play. Misha sits next to Jensen, so he scoots a little bit away from Danneel and puts his arm around the back of Misha’s seat. They share a blanket.

“Sunset’s beautiful,” Misha says as he looks over his shoulder out toward the skyline.

Jensen turns too, taking his arm away from the seat so he can get all the way around. He then fishes his phone out of his jacket pocket and holds it out to Danneel. “Hey, Dee, take a picture of us.”

“Weren’t you complaining, like, five minutes ago about Misha taking too many pictures for Twitter?” Danneel asks even as she takes the phone and holds it up for a photo. “Do you want the sunset in the background?”

“Yes, please,” Jensen replies. He lifts his arm to put it around Misha again but then immediately aborts the movement. “I wanna put this on Twitter,” he whispers.

“You put your arm around me all the time in public,” Misha replies.

“OK, on the count of three,” Danneel interrupts.

As she counts down, Misha says, “Maybe people will be distracted by your dumb hat and won’t notice how gay this picture is.”

For some reason, that makes Jensen burst out laughing. Danneel snaps the picture, and it’s perfect. Jensen stares down at his phone at the picture, Misha huddled close next to him so he can look at it, too. Neither of them say anything for a second.

“You look really good,” Misha says.

“So do you.” Jensen turns just enough to give Misha a kiss on the lips.

“Eww!” West calls from the other end of the deck. “Dad and Uncle Jensen kissed!”

Jensen and Danneel look at each other in confusion. Before they can ask, Vicki explains, “He started doing that recently. I have no idea where he picked it up from, it’s annoying. You can’t even kiss on the cheek without him freaking out.”

“Yeah, here, watch this,” Misha says before leaning over and kissing Jensen’s cheek.

And sure enough, West yells, “Gross!” and sticks his tongue out at them.

“Huh. Weird,” Jensen says as he puts his arm back around Misha.

A second later, J.J. runs up and jumps into Jensen’s lap. He just barely catches her and turns her around so she’s sitting properly on his thighs. She reaches over to the space between Jensen and Misha and grabs his phone.

“Oh, oops,” Jensen says as he tries to take it from her. “Guess I missed my pocket. Can I have that, sweetheart?”

J.J. easily hands the phone over, and Jensen holds it out so both of them can look at it. “You like this picture of me and Uncle Mish?”

J.J. nods enthusiastically.

So Jensen goes ahead and posts it to Instagram and Facebook.

“Y’all aren’t even trying to be subtle,” Danneel says. “You’re, like, showing off that you’re hanging out with each other.”

“Yeah, have you even taken any pictures of the kids? This is gonna look like you took a boat trip alone together,” Vicki adds.

Jensen rolls his eyes and leans his head against Misha’s shoulder, shifting J.J. just a little bit as he goes.

Misha wraps an arm around him and pulls him close. “Maybe if you’d let me post pictures of you, we wouldn’t have this problem,” he says to Vicki.

She glares at him.

Jensen’s not sure how the conversation goes after that. His eyes are closed and he’s holding J.J. tight against his chest as if she’s a blanket. Misha is rubbing his hand in slow circles against Jensen’s sleeve, and their voices drift right over him. He only falls about half asleep, but after way too short of a time Misha shakes him awake and it’s pitch black outside. It’s time to go back. 

Danneel took a picture of Jensen, Misha and J.J. while Jensen was asleep. He doesn’t post that one on social media, but he looks at it for a long time.

Once they’re all back in the minivan, Misha tells the kids that they’re spending the night at grandma’s house. Even J.J. is excited by the news, despite the fact that she’s only met Misha’s mom a couple of times. They don’t waste a lot of time once they get to her house, only going inside to drop off the kids’ stuff and give directions about their schedules.

By the time they make it back to Misha and Vicki’s house, Jensen is wide awake. He grabs a couple of beers from the cooler that they had on the boat and joins Danneel, Vicki and Misha in the living room. Misha is huddled over the coffee table with a comically large bag of weed, and he looks up and winks at Jensen as he takes a seat on the couch next to Vicki.

“Shit, I forgot I asked you to get that,” Jensen says before taking a swig of his beer.

“The guy at the dispenser knows me by name,” Misha responds. “I don’t even smoke weed, and the guy _knows me by name.”_

“Maybe he watches the sh—”

“He doesn’t watch the show, Jensen.”

Danneel laughs, and it’s only then that Jensen realizes she and Vicki are huddled together drinking wine and whispering about something. He narrows his eyes at his wife. She ignores him.

A few minutes later, Misha makes Jensen and Danneel go outside to smoke, which is obviously fine, but Jensen pouts a little when Misha doesn’t come out to join them.

“What were you and Vicki talking about?” he asks as he leans up against the porch railing next to Danneel.

“Just the kids. She said they’re probably done having them. Don’t you think that’s surprising?”

“Not really. Pretty sure Mish told me once that he just wanted two kids.”

Danneel takes a big hit and asks, “And you remembered that?”

“Shut up.”

Smoke puffs out of Danneel’s mouth as she laughs. “You still want more, right?”

“Of course,” Jensen responds, a bit miffed. “You know that.”

“Yeah, I know. We’re just...not getting any younger.”

“What, you want another kid _now?”_

“No! I mean. I don’t know. I know we talked about having two or three, but at this point, if we go for three then I might be pregnant in my 40s.”

Jensen smiles at her. “You only do this when we get high.”

“What?”

“Worry about our future. C’mere.” He grabs her by the hip and pulls her flush against him. “I’m trying to get laid tonight, honey.” He leans down and kisses her. “I don’t want to think about you being pregnant at all.”

She wraps her arms around his neck and kisses him again. “Who do you want to fuck tonight, me or Misha?”

He hums and squeezes her ass. “I have an idea, actually.”

“Oh, yeah?”

The door opens, and Misha pops his head out. “How’s it going out here?”

They turn slightly toward Misha, but Jensen keeps a hand on Danneel’s ass. “Fine, buddy, we’ll be in soon.”

Misha winks at them and then goes back inside. Jensen watches him through the glass.

He only stops staring when Danneel says, “Yeah, you’re gonna fuck _him_ tonight.”

When they get back inside, Danneel shoves Jensen toward Misha and then goes over to sit by Vicki on the loveseat. Apparently Misha and Vicki were sitting on different couches, just drinking wine and talking. Jensen briefly wonders how long he and Danneel have to be together before he can sit in a room with her and _not_ need to touch her.

“Hi, Jensen,” Misha says in a dorky, flirty voice as he reaches his hand out and coaxes him closer by scratching at the back of his neck.

“Hi, Misha,” Jensen imitates. He presses a hand to his thigh and noses at his neck. “How are you?”

“Oh, much better than I was earlier,” Misha responds around a sigh. He puts his hand on Jensen’s back and holds him tight.

“You were in such a bad mood.”

“Yeah, well, I don’t really like feeling emasculated.”

Jensen stops his ministrations and looks very seriously at Misha. “Emasculated?”

“Well. Yeah. You’re way better at boating than I am. I should’ve let you be in charge.”

“Wait, did you invite me out to _impress_ me?”

Misha rolls his eyes and drinks his wine.  

“Mish.”

Misha looks at him, his expression bored.  

Jensen gets right up close to his ear and whispers, “You were hot as fuck today. And I love when you don’t know how to do something perfectly. Makes me feel like I actually deserve you.”

“No, don’t do that.”

“Do what?”

“Make me compliment you. Reassure you that you do, in fact, deserve me. That actually, in reality, _you’re_ the one who’s way out of my league and it still baffles me that you—”

“Mish.” Jensen squeezes his knee. “I didn’t want you to say any of that.”

Before Misha can answer, Jensen kisses him. It starts slow and soft, but after a few seconds Jensen feels his whole body tense in anticipation of what’s to come, and he can’t help but push Misha back onto the couch and lay himself over him as they make out.

A hand that isn’t Misha’s—even high, Jensen _knows_ Misha’s hands—slides its way up Jensen’s back and rests on his shoulder. Frustrated, he pulls away from Misha and is surprised to find Vicki standing above them, smiling down at them with her glasses slipping down her nose.

“It’s time, Jensen,” she says.

He nods and climbs off of Misha. He then reaches a hand down to a very confused Misha and helps him up off the couch. As they head upstairs, Danneel eagerly follows behind them asking in a hushed tone what exactly it’s time for.

Jensen is nervous, but he’s glad his wife is in good spirits. He knows, logically, that it’s stupid how long he and Misha have been together and not included Vicki in any aspect of their relationship. Well, really it’s just him who hasn’t included her. It’s just that the thought of being physically intimate with anybody other than Danneel and Misha is totally foreign to him.

“Jensen, what’s going on?” Misha asks seriously as all four of them walk into the master bedroom.

“Nothing, babe. Relax.”

“Are you OK? We don’t usually…”

Jensen gives him a kiss to reassure him. He then pats his face and says, “Take your clothes off.”

Misha still looks concerned, so Jensen turns his attention to Danneel and grabs her by the hips to kiss her. She reaches for his belt buckle while he pulls her shirt up and tries to get it over her head. She’s wearing a necklace, which gets caught as the shirt is over her face, and they both laugh like idiots.

“Why’d we let them get high,” Vicki says as she comes over to help Jensen and Danneel out of their clothes. She’s clinical with Jensen, giving him a wink while she unbuttons his fly.

Jensen keeps his boxer briefs on as he makes his way back over to Misha, who is completely naked with his neon orange underwear at his feet.

Misha has the fucking nerve to smile shyly at Jensen right before Jensen grabs his love handles and kisses him hard. He walks him back toward the bed, and they trip over each other’s feet until they hit the mattress. If it weren’t for the hard press of Misha’s cock against his stomach, Jensen’s pretty sure he’d be content to just lie here and kiss all night long.

But then Misha’s hands are pushing his boxers down slowly and Jensen loves this part. The part where Misha trails his fingers down his legs and then back up to his sides, over his back, digging in, claiming him with those perfect fucking hands of his.

“What are you thinking about?” Misha asks, his eyes hooded but focused on Jensen.

“Your hands.”

Misha snorts a laugh. “Really?”

“Uh-huh. You have the best hands.”

“Mmm. OK.” He squeezes Jensen’s ass then draws one hand up to run over his cheek and through his hair. He then reaches between them and wraps his fingers loosely around Jensen’s cock. “You like when I touch you?”

“Uh-huh.”

“Because of my hands?”

“Yeah.”

“Huh.”

Danneel gasps from the other side of the room. Misha tries to lift his head to see what’s going on, but Jensen rolls his hips against him and mouths at his jaw.

“What’s going on?” Misha asks again.

“Roll over.”

Misha sighs but rolls over anyway. As soon as he’s on his stomach, Jensen kneads his ass and tells him he’ll be right back with the lube. He drops a kiss to his asscheek and heads over to the nightstand.

Vicki and Danneel are in the bathroom, and when Jensen looks over and spots them through the sink mirror, Vicki makes eye contact with him and then shuts the door.

“Where did our wives go?” Misha asks when Jensen gets back to the bed.

“Bathroom. They’ll be back soon.” Jensen coats his fingers in lube and slides one easily into Misha’s hole.

“Oh, Jesus.”

Jensen takes his time. It’s been awhile since he’s gotten to do this, so he’s going to enjoy every second of it. The way Misha comes undone beneath him will never get old. He puts his full trust in Jensen, which is hotter than anything else about their sex life.

The door to the bathroom opens when Jensen is three fingers deep. Only Vicki comes out of it, though. She stares intently at Misha’s ass as she walks over and sits on the edge of the bed. She’s still fully clothed.

“He can take it deeper,” Vicki says. She reaches a hand out and rubs Misha’s shoulder. “Just crook your fingers up, they’ll go in all the way.”

Jensen does as he’s told, and Misha clenches and shouts a “fuck” in response.

“Where’s my wife?” Jensen asks Vicki, making direct eye contact with her as his fingers move in and out of Misha.

“She’ll be here in a minute.” Vicki crosses her legs. “He’s ready.”

“But I’m barely—”

“She’s right,” Misha interrupts, his voice strained. “I’m—” He cuts himself off with a sigh and then finishes with, “Definitely ready.”

Jensen gives Vicki a look as he pulls his fingers out and wraps his left hand around his cock, and her eyes rake down and back up his body before she nods encouragingly at him. It’s weird having her involved, but Jensen knew when they talked about it that this would be the capacity he could handle. He didn’t want to be the one to bring it up, but luckily she had done it for him. Started the conversation right off the bat by telling him he obviously has a kink for people watching him fuck, and she’d happily fill the role of the voyeur. It took a little bit more convincing than that, but he knew he’d agree to it the moment she mentioned it. Jensen had not told Misha about the conversation, and by the looks of it Vicki didn't tell him either. 

Even so, it’s a little nerve-wracking to have her as an audience. He knows—Misha’s told him as much—that she and Misha have a better, kinkier sex life than he and Misha do. It’s hard not to imagine her sitting there taking notes on what he does wrong so she can debrief with him about it later.

“Any day now, Jens,” Misha says.

Jensen snaps out of it and lubes up his cock. He gives Misha’s ass a little pinch and then pulls him back toward him so he doesn’t have to climb up onto the bed to mount him. He feels a lot better, a lot more grounded if he stands. He gives Vicki one last look before pushing in. She bites her lower lip as she watches.

When Jensen starts moving, Misha makes all kinds of noises, thrusts back to meet him, grabs his wife’s hand and squeezes it hard. Vicki and Jensen both shower him with encouragement, which only makes him more vocal and needy. It’s so good that Jensen almost forgets the other surprise and jumps a little when a hand comes up over his shoulder.

“Hey, baby,” he says, turning his head so he can give his wife a kiss.

“Climb up on the bed,” she replies softly.

“Oh, hey, Danneel,” Misha says sarcastically. “No, you’re not interrupting anything. Please, join us.”

Vicki runs a hand through Misha’s hair and shushes him. “You’d change that attitude if you could see her right now,” she says.

Which, of course, makes Misha try to turn all the way around to get a look. He clenches at an awkward angle around Jensen’s cock, so Jensen quickly pulls out and clambers up onto the bed. He presses his hands to the sheets on either side of Misha and then slowly lowers himself back down and is pleased this time when Misha clenches around him.

“Wait, what’s Danneel doing? What’s happening? Please someone tell me what’s going on,” Misha complains. Then, after a second, he gasps and exclaims, “Oh! Is it happening? The thing I’ve always wanted, is it happening?”

“Yeah, babe, it’s happening,” Jensen replies between stilted breaths.

Danneel has three fingers in his ass and is not taking her time. Jensen’s glad, too, because he’s definitely not going to last much longer.

Misha grips Vicki’s knee and then slaps it a few times. “Tell me what’s happening. Describe everything.”

“Well, Jensen is pressing into you and then pushing back against Danneel’s fingers,” Vicki says evenly. “Danneel is wearing a 9-inch strap-on with veins. I think it might glow in the dark, too.”

Jensen just barely manages to raise his head and roll his eyes at her.

“And now Danneel is getting up on the bed.” Vicki laughs. “She’s making a face because she has to spread her legs really wide to get over both of you guys.”

“How the hell am I supposed to do this?” Danneel asks.

“Just lower your hips down, sweetheart,” Vicki encourages. “You can stay on your knees. Yeah, that’s good.”

“OK. Ready, Jens?” Danneel asks, both her hands massaging his ass.

“Yeah, go for it,” he answers as if this isn’t the biggest fucking deal in the world.

The only person who’s ever really, properly fucked Jensen is Misha. So his only frame of reference is the way Misha teases his hole with the head of his cock before sliding in smoothly in one practiced motion.

Danneel, however, pushes about an inch in then pulls back out, pushes two inches in and pulls one inch out, in, out, etcetera until the dildo is in as far as it’ll go.

“Oh my god,” Misha says. “The weight of this is amazing.”

Jensen tries to keep a steady rhythm in and out of Misha, but his wife is pounding into him and making the whole bed shake, so all three of them are out of sync.

“This is...exactly how I always imagined it,” Misha continues even as his face is repeatedly pushed deeper into the mattress. “I can feel you, Dee.”

Danneel reaches a hand between Jensen and Misha and tickles Misha’s ass. “I’m here, babe,” she says to him.

“Fuck him real good and hard for me.”

A tingle runs through Jensen’s body at the command. He fucks Misha a little bit faster after that, which makes both Misha and Vicki laugh.

His orgasm happens fast. One second he’s focused on pushing in and out of Misha and the next second Danneel is pounding his prostate and he comes deep in Misha’s ass. Almost immediately after, Misha shouts and clenches.

“Shit,” Misha says between panted breaths.

Jensen collapses against his back and puts his face on his shoulder. “Did you just come untouched?”

“Maybe.”

Danneel slips the dildo out of Jensen’s ass and removes the harness. She hands it over to Vicki and then lays herself flat against Jensen’s back, pulling an “oof” out of Misha.

“That was quicker than I hoped it’d be,” Vicki says.

“Sorry,” Jensen replies.

“Babe, Vicki and I are gonna take the guest bedroom,” Danneel says hurriedly, somewhat out of breath. “Neither of us came just now, so we’re gonna...take care of that. Y’all can deal with the come-stained sheets.”

“Great.”

Danneel kisses Jensen between the shoulder blades and then her weight is gone. He rolls off of Misha and suddenly feels really exposed with his flaccid dick out there for everyone to see. He looks at Vicki, and she seems to read his mind and averts her gaze as she gets up from the bed.

“Don’t stay up too late,” Vicki says as she takes Danneel by the hand to lead her out of the room.

Misha sits up urgently and says, “Victoria.”

Both Vicki and Danneel turn to look at him.

“Thank you,” is all he says.

When the girls are gone, Jensen curls up against Misha’s side and mouths at his jaw for a second. With his mouth against his skin, he asks, “Did you have any idea that was happening tonight?”

“No.” Misha pulls Jensen closer and kisses his forehead. “I know she intimidates you, but thank you. I really enjoyed having her here.”

“Thank _you_ for one of your fantasies being Danneel fucking me.”

Misha huffs a laugh. “I’ve been picturing that for...god, I don’t know. Both of you are so hot.”

Jensen climbs on top of Misha and buries his face in his neck, kissing and biting and rolling his hips until Misha is laughing and clutching at his back.

“We’re lying directly on top of my come,” Misha says. “Can we please shower?”

Jensen kisses him on the lips. “Together?”

A smile pulls at Misha’s lips. He reaches a hand up and cups Jensen’s face. “You’re obsessed with me.”

“Shut up.”

“Hey.”

“Hmm?”

“I love you.”

Jensen rolls his eyes and then kisses him again. “Yeah, yeah, I love you, too.”

**Author's Note:**

> Here are links to [Jensen](https://youtu.be/yCmw5YsxSw0?t=100) and [Misha's](https://www.youtube.com/watch?v=TxlsPYpgk1w&t=205s) accounts of this story. I had Maison get sick mainly because we never got any pictures of anybody other than Jensen, Misha and West so......who knows who was actually on this trip. Also, I took out West playing with (torturing) crabs for, uh, reasons. 
> 
> Here are pictures - [(1)](https://s-media-cache-ak0.pinimg.com/736x/b8/75/3a/b8753a9307b9ea1fcd3bb07e20ba1378--boats-good-ideas.jpg) [(2)](https://twitter.com/mishacollins/status/634909862061719553) (3)
> 
> This is officially the end of When Harry Met Sally. I MIGHT sometime in the future be posting a bibliography for all the real events included in this series. Thank you again to [Charlotte,](http://casthegrumpy.tumblr.com/) my editor, without whom this story would've never been published. 
> 
> I'm [deancasheadcanons](http://deancasheadcanons.tumblr.com/) on tumblr, and this is [my website.](https://maddmadeshop.com/)


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